Inspiration From Sterling Point: Looks For Fall

The girls of Sterling Point felt like people we already know, and their closets told you who they were before they said a word.

Summer has been fun, and thanks to Prime Video with their slate of great shows and movies, we got to do a lot of traveling. But one place we really loved visiting was Muskoka. Sterling Point was one of our favorite shows of the summer because it takes family, friendship, and finding yourself seriously. The girls at the center of it are some of the most relatable characters we’ve seen in a teen drama in a long time.

It doesn’t matter whether you see yourself in Annie, Ramona, or Oona. Each of them has something you’ll recognize. And you could find yourself in their clothes too, because costume designer Marissa Schwartz built every wardrobe to feel true to the person wearing it. Laid-back, preppy, or all about comfort, the fashion in this show is relatable, and it’s never just decoration. It’s character.

Annie – the girl with the plan

Annie is the planner. She gets rejected from the summer program she’d built her future around, and then finds out the grandfather she was never allowed to meet left her an island in Canada. If you’ve ever had a plan fall apart and had to work out who you are without it, you know Annie.

Her clothes start out as armor. She shows up at a lake in an all-white travel outfit and silk outerwear, which is the most city-girl choice possible. Schwartz has said Annie is “very parentified,” someone who took on the matriarch role in her family, so they gave her polished, serious clothes. She dresses like she’s already a twenty-something with an important office job. That’s what I love: the Chanel watch isn’t about showing off. It’s what a girl wears when she’s decided she has to be the adult.

Then Muskoka gets to her. As the season goes on, she starts wearing Ramona’s clothes, thrift finds, and loose, colorful cottage wear. Ella Rubin described it as dressing for “the way that she wanted to feel, rather than the person she wanted to be perceived as”. That’s her whole arc in one line. Annie literally wearing the clothes of the people she’s getting close to is the show’s way of saying she’s letting them in.

Ramona – the girl who stayed

Ramona grew up on the island, and she’s protective of her home and her history. Then Annie shows up with a claim to it. If you’ve ever felt like someone new was about to take up the space you’d worked hard to make yours, you know Ramona. She isn’t really prickly. She’s scared, and she hides it behind her boundaries.

Her wardrobe was designed to reflect someone fiercely independent who has been taking care of herself for a long time: thrifted, functional, lived-in. Ramona’s style was described as, “cottage sweatpants as pieces she’s worn a million times, with the drawstrings completely unraveling, and she still reaches for them every time. Oversized silhouettes, baggy tops, low-rise shorts, keys hanging off her belt loop.”

There’s a lesson in that. Ramona doesn’t dress to be looked at. She dresses like someone who has never had the luxury of performing. Put her next to Annie and you see the whole show: one girl dressed for the future she planned, one dressed for the life she’s actually living. Each of them has what the other never got.

Oona – the one who holds it all together

Oona is bold, flirty, and funny, and she’s also taking care of her younger sister. If you’ve ever been the one keeping everyone laughing while carrying more than anyone knows, you know Oona.

Her clothes are the loudest on the island, on purpose. She is a free spirit, using graphic tees that showed her sense of humor. Her wardrobe that feels collected over years of traveling with her mom and landing in different places. Printed tops, bikinis, camo, and a ton of vintage, plus a stack of silver rings.

Oona’s style is a travel diary. Every piece comes from somewhere she’s been. For a girl who has had to be a bit of a parent herself, the joke on her T-shirt is doing a lot of the emotional work.

Why these girls land

What makes these characters relatable isn’t that they’re perfect. It’s that their clothes and their choices come from the same place. Annie dresses for control until she learns to dress for comfort. Ramona dresses for survival. Oona dresses for joy because joy is how she copes. And the show lets every one of those choices mean something.

That’s the romanticize-your-life part of Sterling Point. It makes a lake summer feel like somewhere you could actually go, and it makes getting dressed feel like telling people who you are. The show isn’t asking you to pick one girl. It knows you’ve been all of them at different points in your life

As we transition into fall, we’re showing you some outfits that you can make your inner Annie, Ramona, or Oona shine.